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13,14-Dihydro-15-keto-PGF2α

Cat No.:V71117 Purity: ≥98%
13,14-Dihydro-15-keto PGF2a is an endogenously produced metabolite present in the blood and may be utilized to study pregnancy.
13,14-Dihydro-15-keto-PGF2α
13,14-Dihydro-15-keto-PGF2α Chemical Structure CAS No.: 27376-76-7
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
13,14-Dihydro-15-keto PGF2a is an endogenously produced metabolite present in the blood and may be utilized to study pregnancy.
13,14-Dihydro-15-keto-PGF2alpha (also known as PGFM) is the principal plasma metabolite of prostaglandin F2alpha (PGF2alpha), formed through sequential oxidation by 15-hydroxyprostaglandin dehydrogenase (15-PGDH) and reduction by delta¹3-reductase. This compound is an endogenous metabolite present in blood and is utilized as a biomarker for in vivo production of PGF2alpha, particularly in studies of pregnancy, parturition, and reproductive biology.
Biological Activity I Assay Protocols (From Reference)
Targets
No specific drug target; serves as an endogenous metabolite and biomarker for PGF2alpha production. May bind to bovine acetylcholinesterase and potentially other plasma proteins.
ln Vitro
Endogenous metabolites are those that the Kyoto Encyclopedia of Genes and Genomes has identified as products or substrates of the approximately 1900 metabolic enzymes that are encoded in human genome. Numerous of these metabolites have been shown to have harmful effects, as evidenced by the body of literature [1].
13,14-Dihydro-15-keto-PGF2alpha is the first prominent plasma metabolite of PGF2alpha. It is an endogenously produced metabolite present in the blood and may be utilized to study pregnancy. It has been shown to bind to bovine acetylcholinesterase. As a metabolite, it exhibits significantly reduced biological activity compared to its parent compound PGF2alpha.
ln Vivo
As a metabolite, 13,14-Dihydro-15-keto-PGF2alpha is used as a biomarker to assess in vivo production of PGF2alpha. Measurement of PGFM levels in blood and urine serves as an indicator of PGF2alpha release in various physiological and pathological conditions, including pregnancy, parturition, inflammation, and reproductive disorders. Elevated levels may indicate increased PGF2alpha synthesis.
Enzyme Assay
Receptor binding assays are not applicable for this metabolite as it has low biological activity. Standard analytical protocols for measuring 13,14-Dihydro-15-keto-PGF2alpha in biological samples involve immunoassays (EIA or RIA) or LC-MS/MS. For LC-MS/MS, samples (plasma, serum, or urine) undergo solid-phase extraction, separation on a reverse-phase C18 column, and detection in negative ion mode with MRM. For EIA, kits specific for this metabolite are used.
Cell Assay
For cell-based studies, cultured endometrial, myometrial, or placental cells may be treated with PGF2alpha (1-100 nM) for 1-24 hours, and culture medium is analyzed for 13,14-Dihydro-15-keto-PGF2alpha accumulation by EIA or LC-MS/MS to assess 15-PGDH and delta¹3-reductase activity. The metabolite itself is not typically used as a treatment in cellular assays.
Animal Protocol
In vivo animal studies using this compound are typically conducted for pharmacokinetic or biomarker studies. Rodents are administered PGF2alpha (intramuscular or intravenous, 0.1-1 mg/kg), and blood samples are collected at multiple time points (0-6 hours). Plasma levels of 13,14-Dihydro-15-keto-PGF2alpha are measured by EIA or LC-MS/MS to quantify PGF2alpha clearance and metabolite formation. Alternatively, endogenous levels are measured in pregnancy models.
ADME/Pharmacokinetics
13,14-Dihydro-15-keto-PGF2alpha is a circulating metabolite that is rapidly formed from PGF2alpha following its release. The conversion occurs primarily in the lungs, liver, and kidneys via 15-PGDH (which reduces the 15-hydroxyl group to a 15-keto group) and delta¹3-reductase (which reduces the 13,14 double bond). The resulting PGFM has a longer half-life than PGF2alpha (approximately 10-20 minutes vs. 1-2 minutes), making it a more stable biomarker.
Toxicity/Toxicokinetics
As an endogenous metabolite, 13,14-Dihydro-15-keto-PGF2alpha is not toxic. It is normally present at low concentrations in healthy individuals (typically <20 pg/mL in plasma). Elevated levels reflect increased PGF2alpha production, which is associated with physiological processes (parturition, menstruation) or pathological conditions (dysmenorrhea, endometriosis, inflammation).
References

[1]. Endogenous toxic metabolites and implications in cancer therapy. Oncogene. 2020 Aug;39(35):5709-5720.

[2]. The dynamic changes of several reproductive hormones during termination of early pregnancy by RU486 in combination with PG-05 in Chinese women. Adv Contracept. 1988 Dec;4(4):319-26.

Additional Infomation
13,14-Dihydro-15-keto-PGF2α is a prostaglandin Fα obtained by formal oxidation of the 15-hydroxyl group of prostaglandin F2α and hydrogenation of the 13,14-double bond. It is a metabolite. It is both a prostaglandin Fα and a ketone. Functionally, it is related to prostaglandin F2α. It is the conjugate acid of 13,14-dihydro-15-keto-PGF2α(1-).
13,14-Dihydro-15-keto-PGF2alpha (PGFM) is an endogenous metabolite and research biomarker, not a therapeutic agent. It is the stable end product of PGF2alpha metabolism and is widely used in reproductive biology research. Its measurement is used to monitor spontaneous or induced labor, to study luteolysis in animal models, and to assess PGF2alpha production in inflammatory conditions. This compound has no approved clinical indications for therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H34O5
Molecular Weight
354.48
Exact Mass
354.24
CAS #
27376-76-7
PubChem CID
5283039
Appearance
Colorless to light yellow liquid
Density
1.1±0.1 g/cm3
Boiling Point
543.0±40.0 °C at 760 mmHg
Flash Point
296.2±23.8 °C
Vapour Pressure
0.0±3.3 mmHg at 25°C
Index of Refraction
1.512
LogP
2.13
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
13
Heavy Atom Count
25
Complexity
432
Defined Atom Stereocenter Count
4
SMILES
CCCCCC(CC[C@H]1C(O)CC(O)[C@@H]1C/C=C/CCCC(=O)O)=O
InChi Key
VKTIONYPMSCHQI-XAGFEHLVSA-N
InChi Code
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,18+,19-/m1/s1
Chemical Name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8210 mL 14.1052 mL 28.2103 mL
5 mM 0.5642 mL 2.8210 mL 5.6421 mL
10 mM 0.2821 mL 1.4105 mL 2.8210 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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